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A
Hey, everyone, it's me, Sam Stein. I'm here with Will Salatin, and we are going to be talking about the White House correspondence makeup dinner that happened last night. We're recording on Saturday morning. Dinner happened last night at the Waldorf Astoria. And I'll just cut right to the chase. Trump bombed, like, really badly. Really badly. Though I'm not going to say it was a complete disaster, because there are a few jokes that I thought were pretty funny, but he bombed, like, legitimately. It was uncomfortable and the pan away shots all told the story. But, Will, what happened?
B
Oh, Sam, we can, we can have a debate because your position is he didn't completely bomb, and my position is he completely bombed.
A
But I gave him credit for one or two jokes.
B
You're a generous guy. So that's, that's. You could you. You can play. So there's an expression in comedy world. He died on stage, and that is what happened to Donald Trump. So it was like the jokes were bad. The jokes, by the way, the main point, and we can go into this, the jokes were mostly racist, sexist, homophobic, Islamophobia. It was. It was terrible. It was your old racist uncle kind of thing. So it was really. That. It was terrible. But also, but also the laughter stopped because even the MAGA people in the audience recognized that it was bombing. And so Trump recognized. He saw that it was painful to him.
A
Yeah. You knew it was going bad, and you knew Trump knew it was going bad because on several occasions he was just going on. He was doing meta analysis. Who wrote this?
C
He was.
B
He was like, you know, that's how you know you're dying when you're explaining the joke. Except a professional comedian knows not to explain the joke because it just makes it worse. It was super painful. Several times there was this joke he
A
told about seniors and senators walking upstairs. Did you see that one?
B
Yeah. Yeah, absolutely.
A
Let's play it.
C
I do think we need term limits in Congress. I think term limits are very important because I see what's happening. I see what's happening. The other day, a senator I knew got a text, a great guy from his wife, and she said, when you get home, I want to have you immediately come up the stairs and make love to me. And he said, I can't do both. You know what? You know, in other words, you can't go up the stairs and make love. Does anybody get that? Well, I thought that was actually pretty good. That was actually the only thing I thought was good in this whole fricking stupid speech that they wrote that was the only good one. And that went down with not exactly great laughter, I think, you know, in other words, you can't go up the stairs and make love too, you know, so we're looking for term limits. Does anybody understand this now?
A
Yeah. When you have to explain in that type of granular detail what you meant. It's both, you know, it was just painful. He must have been. Well, I don't think he was dying inside because I don't think he has the capacity for that type of shame, but I would have been dying inside.
B
Yeah. So. So he blames, you heard him. So he blames the writers. And, and to be fair to Trump, I. So we, we should be fair. Right. The thing I'll be fair is the writers were bad. They wrote some really bad jokes. But, but also there were several points in this speech where you could tell he was reading the joke and the joke was not great, but he made it so much worse by then ad libbing something mean on top of it.
C
So.
B
So don't blame the writers entirely, Donald. You made it that much worse every time.
A
His delivery was really bad. He's, he can be funny when he's just riffing and being like, you know, Archie Bunkerish, but, like, when he's reading jokes, they don't always land. Can I play you the one joke that I thought was funny?
B
Yeah. Let's hear it.
C
Everyone finally got to enjoy their entire. Very delicious beef tenderloins. Very special beef. And I want you all to know that Bobby Kennedy is right here. Personally ran over the cow in his
A
car
C
and he cut it up and he brought it here for you to eat tonight. So it's very fresh. And Bobby also suggested an appetizer featuring his favorite cut of male raccoon roadkill. But we drew the line at that, Cheryl. We said, no, we're not going to do that.
A
Okay. Come on. Yeah, you're laughing.
B
I'll give you that one, Sam. That actually, that was the highlight of the show. And that was pretty early on that he did the Kennedy joke. It was, yeah, that was, that was the best joke he gave. But Sam, it's kind of interesting because to me, that joke is the closest thing to a traditional correspondence dinner joke. Right. It's self deprecating. It's about somebody in my administration. And like, it's, it's, it wasn't mean, you know, it was like one of his guys, but about something that he, that Kennedy himself has joked about. So that, that was the problem is that the rest of the Speech just wasn't like that.
A
Yeah. The problem was his speech was basically a Trump speech. Right. Like, it just didn't make. Let's put the. Like, he took shots at everybody. Gavin Newsom, Jimmy Fallon, Stephen Colbert, like, joked about having a third term, which you call the fourth term, because he really run, you know, blah, blah, blah, blah, blah. And then there's just, like, random asides like, let's play the Nicki Minaj one, which was just. It just felt unnatural coming from Trump's mouth.
C
Hearing the gunshots, many people yelled, get down. Get down. Which caused Nicki Minaj to start twerking. Do you believe get down. She's the only one that really understood what that meant. Quite an evening.
A
It's quite an evening. And that was like, fine. But it just. The delivery's so bad.
B
He screwed it up. Like, Sam, can you imagine if Obama. If Obama were delivering that joke, it would have been funny. He would have, like, got the timing right, and Trump just, like, killed it with the. So even. Even the best jokes he had, or the least bad jokes, he screwed up with the delivery.
A
Yeah, just one on the delivery front. Doing a lot of clips for this, but. So there was a good Barry Weiss joke that could have been made really funny, and he just butchered it. And I'll. Let's play this, because this is like, there was a funny setup here. And he just kind of. To your point, he's just reading the prompter. If it felt like he didn't even rehearse this thing prior to delivering the speech. Let's read the bear. Let's do the Barry Weiss clip.
C
I have to say that we're having an amazing.
A
He really is reading.
C
Load of accomplishments that the media never talks about. For example, under my administration, a once feared and powerful regime that relentlessly attacked America has finally been toppled. Their former leaders have been removed, and they're now being run by a gay dictator facing internal divisions. But I, for one, wish Bari Weiss all the best at CBS News. She a wonderful woman.
A
Oh.
B
So I couldn't laugh at some of these because by the time he got to this joke, he was. He had, like, done so many slurs, ethnic slurs, homophobic slurs. He. He went. He went at Anderson Cooper before that and said something about. Anderson Cooper is a. What? Different. Different persuasion from me. Like, he was. He was doing some gay stuff. So the. The Weiss joke would have been funny if people understood Donald Trump to be a friend of gay people. But instead, like, with all the transgender stuff, it just comes across as Mean, yeah.
A
And I. And that was the problem for a lot of this. And this is where we turn to a more serious tone. He was just a jerk. And he said things on the stage that, you know, maybe you can be sort of slap stick about it, and maybe you can be like, you know, what's the comic dog insult? The triumph. The insult? Yeah, maybe. Yeah, you can do that. But, like, he didn't do that. He was just an. And he said things that were deeply uncomfortable at times. Never more so for me. I. I remember the Anderson Cooper one actually did stand out to me. But I thought the. The comment about Caitlin Collins, who he clearly, like, has a thing with. Like, he. She just. I. I don't know. She got presented an award. And, yeah, he talked about her in ways that I thought were so misogynistic and nasty in the room. I would have been incredibly uncomfortable. And I guess it's worth playing so that people know what we're talking about.
C
Want to personally congratulate CNN's Caitlin Collins on receiving. Her award was all about me. It's a fake. She shouldn't get the award. It was a fake. But I didn't mind. I said, caitlin, congratulations. But it was fake. There's no question about it. But she's a young, attractive woman. She never smiles. I said, caitlin, do you ever smile? Smile. You have a nice position. You're at CNN fake news. You should be a happy person. So smile, Caitlin, just smile. But we attack. And I thought Caitlin had really made it big with a major new sponsorship. But then I informed her that it wasn't her on the Bud Light can. It was Dylan Mulvaney. And Dylan Mulvaney cost Bud Light $35 billion.
B
Yeah, the shot. Shot at Caitlin, shot at Mulvaney. He took a shot at everybody. The. The sexism. Honestly, Sam, that sexist dig at Kaitlan Collins was the. The least of some of the stuff he did. There was anti. There was anti Muslim stuff. There was anti black stuff. There was. I mean, every disgusting thing you could. Sam. You know, I was trying to think of a comparison of an insult comic or a comic who died on stage doing this kind of thing. And the closest thing I could think of. You and I are old enough to remember this, but a lot of young people wouldn't. I think it's 20 years ago. Michael Richards, the guy who played Kramer, remember this? He did a comedy club, and he just. He gets upset in the middle, and he just launches into this racist tirade. And at first, people think he's just trying to be funny, and then they realize, no, no, no, this guy's really angry and bitter and mean, and that's. That's what Trump was last night. I mean, the. The venom just came out.
A
Yeah. And what's. What's disturbing is that so many people in. In the maga sphere are, like, right on. Stick it to him. This is great. He's going into the lion's den, and he's just, you know, mocking them and. And launching bombs on them and all. And, like, they. They kind of eat it up. Right? They. They find the insult, they find the misogyny, they find the anti LGBT stuff great. And I look at it, and it makes my skin crawl. I. I know that there's other things you pointed out, but to, like, take a moment of professional triumph for Kaitlan Collins and to try to reduce her into a pretty little girl who doesn't smile enough, and maybe I'll compare her to a transgender influencer, like, that's about as low as it gets to me, like, that. That you have to be a really small human being to do that in that moment. And that's what really stood out.
B
Yeah. And a lot of these are lines that, as you said, he uses them in his rallies and what he's done just to have some perspective on this whole thing. Donald Trump has created a world where he has rallies, where he's brought some of the worst people in our country together who share his low sense of humor, and they laugh. And so he's used to the laughter. And part of what happened last night is he had a room that was mostly people who are not like that, and they were. You know, they had a normal ethical sense, and they weren't laughing. And, you know, he didn't get the feedback he's used to. And even the people who supported him realized that he wasn't getting. So it was almost like we had a. For. For just a fleeting moment. We had a normal, healthy culture, people who. Who didn't laugh at these disgusting jokes, and it was painful to him and painful to his supporters.
A
It's such a good point. When's the last time he's ever been in a setting where the audience isn't filled with sycophants? Seriously, I can't. I mean, he went to Joe's Crab Shack or whatever once, and he got yelled at, but, like, that's literally. He's either at his club, where people literally pay to be near him, or he's at the White House, where it's just filled with staffers, or he's at rallies, which are.
The Bulwark Podcast
Date: July 25, 2026
Host: Sam Stein
Guest: Will Salatin
In this episode, Sam Stein and Will Salatin dissect former President Donald Trump’s performance at the previous night’s White House Correspondents’ Dinner, held at the Waldorf Astoria. The episode offers a candid, humorous, and at times searing analysis of what the hosts describe as a “trainwreck” of a speech filled with failed jokes, cringeworthy moments, and uncomfortable silences from an unsympathetic crowd. The hosts debate whether Trump “completely bombed” or if a few “decent” jokes saved the night at all, using real examples and reflecting on the cultural implications of Trump's comedic style.
This episode delivers a nuanced and deeply critical look at how Donald Trump’s self-styled brand of “entertainment” flounders outside his comfort zone. The hosts, with a mix of humor and outrage, reveal how comedy rooted in cruelty and division fails to amuse (or unite) when presented to an audience with “a normal ethical sense.” The result is both a post-mortem on the dinner and a reflection on the state of political discourse, serving as a revealing snapshot of the ongoing clash between Trumpism and mainstream American norms.